Dyeing regenerated cellulose silk



, Patented May 6, 1930 JAMES BAIDDILEY, PERCY CHORLEY, AND RAINALD BRIGHTMAN, OI BLAGKLEY, MAN- CHESTER, ENGLAND, ASSIGNORS TO BRITISH DYES'IUFFS CORIORA'IION LIMITED,

F BLAGKLEY, MANCHESTER, ENGLAND DYEING .REGENERATED CELLULOSE SILK No Drawing. -original application filed May 21, 1927, Serial No. 193,376, and in Germany May 2, 1927. Divided and this application filed July 6, 1928. Serial No. 290,882.

In our copending application Serial No. 193,37 6 of which this application is a division, We have described the preparation of new secondary disazo dyes by coupling diazotized aminoazo compounds, (including their homologues, derivatives and the sulphonic or .carboxylic acids thereof in this term) in alkaline or acid media with sulphonic acids of 2-amino8-naphthol of the type 'OH H wherein R, represents alkyl or acyl group or benzene or naphthalene residue which are free from amino substituent. r The secondary disazo dyestuffs produced by this method are characterized by the following general formula wherein R represents a benzene or-naphtha- -lene residue and R represents a coupled Q-amino-S-naphthol sulphonic acid. of the type 1 OH H i so ow wherein R represents alkyl or acyl group or benzene or naphthalene residue which are free froman amino substituent.

We have found that the secondary disazo 'dyesprepared by the methods disclosed in our acknowledged application Set. No. 193,37 6 and having the above characteristic general formula, possess the valuable property of dyeing regenerated cellulose silks, such as viscose silk, in even level shades. These dyestufis may be applied to a variety of fabrics, for example to wool, cotton or .45 regenerated cellulose silks. Some of these dyestuffs arebetter adapted for one type of fabric or fiber while others are better suited for another type of fabric or fiber. However, the most important, valuable and .surprising discovery is that all of the dyestuffs of this general class will dye regenerated cellulose silks in even level shades. In this resides the most valuable part of our invention. The following description is typical of the application of the dyestuffs of the general class set forth above to regenerated cellulose. Example A.Dyebath is made up from 3,000 parts of water and 6 parts of the dyestuff obtained by combining aminosalicylic acid with u-naphthylamine, rediazotizing and combining with 8-hydroxy-2 2 2-dinaphthylamine-3: G-disulphonic acid. This dyestuff hasin the form of a free acid'the probable formula COOH 7 H0 8 soar:

100 pai'ts of viscose silk are entered into the bath cold, after which the bath is heated up to boil, 30 parts of Glaubers salt are added and dyeing is allowed to proceed at or near to the boil for about hour. Soap may be added to the dyebath if desired. The dyeing obtained is a level deep blue-black shade.

A level brown shademay be obtained in a similar manner by using the dyestufi" ob- I tained by diazotizing p-aminoazobenzene-p'- V sulphonlc acid and coupling it in alkaline solution 2-phenylamino-8-naphthol-6-sulph0nic acid. This dyestuif has in the form of the free acid the probable formula where R represents alkyl or acyl group or examples of dyeings in which the dyestufis and the corresponding shades on viscose silks obtained are quoted in the following table wherein R represents a benzene or naphtha- 'lenearyl residue free from hydroxyl groups and R represents a coupled 2-amino-8-naph- I Aminoazo compound diazotized N-substitution product of Zagmine-B-naphthol sulphonic sci Shade ion viscose silk rp-xylidifip SlilIJhOFgC acid llliiialmlinop-cresol methyl ether minos cy 1c 2101 a-nap y amine Aminoazpbenzene p-aminoazobenzene-p-carboxylic acid p-aminoazobenzene-p-sulphonic acid p-aminoazobenzene-p-sulphouic acid p-aminoazobenzene-p-sulphonic acid p-aminoazobeuzene-p-su1phonic acid p-aminoazobenzene-p'-sulphonic acid p-aminoazobenzene-p-sulphonic acid 2napthtl1y1amiue-4 8-disulphonic acid qz-uaph thylamine Aniline-l-naphthylamine-fi-sulphonic acid 2-phenylamino-8-naphthol-6'su1phonic acid Z-phenylamino-8-naphthol-6-sulph0nic acid Violet-black Black 2-phenylamino-8-naphth0l-6-sulphonic acid Brown 2-phenylamino-8-naphthol-6-sulphonic acid Brown 2o-mcthoxyphenylamino-S-naphthol-fi-sulphonic acid Brown 2-(2 :4-dinitro) phenylamino-8Fnaphthol-6-sulph0nic acid Red-brown Z-ethylamino-8-naphthol-6-su1phonic acid Olive-brown 2benz0ylamino-8maphthol-fi-sulphonic acid Brown 2-acetylamino-S-naphthol-fi-sulphonic acid Red-brown 8-hydroxy-2-11aphthyIglycine-dsulphonic acid Orange-brown Z-phcnylamino8-naphthol-6-sulphonic acid Navy-blue 2-phenylamino-g-naphthol fi-sulphonic acid Blue-black .What we claim and desire to secure by Letters Patent is I 1. The process of dyeing regenerated cel lulose materials in even level shades, which comprises applying to the said regenerated cellulose materials the secondary disazo dyestufi's having the following general formula wherein R represents a benzene or naphthalene residue and R ,.represents a coupled 2zamino-8-naphthol sulphonic acid of the yp wherein R represents alkyl or acyl group or benzene or naphthalene residue which are free from an amino substituent, the said regenerated cellulose materials being thereby dyed in even level shades.

2. As new materials, the regenerated cellulose materials dyed with a secondary disazo dyestufi' having the following formula R--N=N-R-N=N-ic wherein R represents a benzene or naphthalene residue and R represents a coupled 2- amino-8 -naphthol sulphonic acid ofthetype benzene or naphthalene residue which are free from an amino substituent, the said dyed regenerated cellulose material having an'even level shade. V

3. As new materials, the regenerated cellulose materials dyed with a'secgndary disazo dyestuff having the following formula thol sulphonic acid of the type OHH in which R represents a benzene or naphthalene residue and R represents a coupled 2- amino-8-naphthol sulphonic acid of the type OH H wherein R represents alkyl group or'abenzene or naphthalene residue which are free from amino substituents, the said dyed regenerated cellulose material having an even level '7 shade.

5. As new materials, the regenerated cellulose materials dyed with a secondary disazo dyestuff having the following formula R -1 I=NBN=N-R V wherein R represents a benzene residue free from hydroxyl groups, R represents a benzene or naphthalene residue and R represents coupled 2-amino-8-naphthol sulphonic acid the typ v Ikr-Bl wherein R represents alkyl or acyl group (or a benzene or naphthalene residue which are free from amino substituents', the said. dyed regenerated cellulose having an even level shade. o 6. As new materials, the regenerated celulose materials dyed with a secondary disazo dyestufi having the following formula wherein R represents a benzene residue containing a sulphonic or carboxylic acid group, R represents a benzene or naphthalene residue and R represents a 2-a1nino-8-naphthol sulphonic acid of the type vIr [ni -R,

wherein R represents alkyl group or benzene or naphthalene residue which are free from amino substituents andjn which at least one sulphonic acid group is connected to the 2-amino-8-naphthol nucleus in the sixth posi tion, the said dyed regenerated cellulose material having an even level shade.

7 As new materials, the regenerated cellulose materials dyed with a secondary disazo dyestufl having the following formula wherein R represents a benzene or naphthalene re idue and R, represents a benzene or naphthalene residue which is free from amino substituents, the said dyed regenerated cellulose material having an even level shade.

8. As new materials the regenerated cellulose materials dyed with a secondary disazo dyestufi' having the following formula IIOaS a a brown para-phony ene-diamine sulphanilic acid and 7 -amino-2'-phenylan1ino-8-naphtholfi-sulphonic acid, the said dyed regenerated cellulose materialhaving an even level shade. In testimony whereof We aflix our signatures.

JAMES BADDILEY. PERCY GHORLEY. RAINALD BRIGHTMAN. 

